In this article, the author explores the implementation of OECD Pillar Two in Gibraltar, Guernsey, the Isle of Man and Jersey. It begins by outlining the framework’s core rules – the Income Inclusion Rule (IIR), Undertaxed Profits Rule (UTPR) and Qualified Domestic Minimum Top-Up Tax (QDMTT). The author then traces the timeline of each jurisdiction’s commitment to Pillar Two and examines the legislative steps taken to adopt it. Through a comparative analysis, this article highlights key similarities and differences in approach, offering insight into how these jurisdictions are aligning with global tax reform efforts with global tax reform efforts while protecting their tax bases and regulatory autonomy.